The Montreal Canadiens, fresh off a Stanley Cup celebration, went into the 1965-66 season with a strong team and desire to repeat, and finished the season in first place. They met the Toronto Maple Leafs in the semi finals, and made short work of the Leafs, eliminating them in four straight games.

Meanwhile, Detroit and Chicago met to decide who would challenge Montreal for the Stanley Cup. The Red Wings won the series four games to two, to enter the fray for the Stanley Cup.

Detroit won the first two games of the final, with Roger Crozier at his acrobatic best in goal. But Montreal persevered to win the next four straight, and took the series four games to two to win their second straight Stanley Cup.

Henri Richard scored the overtime Cup-winning goal in game six. Although his team lost the final, Detroit goaltender Roger Crozier posted a 2.17 goals-against average in 12 games and was awarded the Conn Smythe Trophy.